Rating:
![question](question.png)
1) text.txt contains:
126-Y, 113-N, 122-N, 130-N, 117-N, 107-N, 137, 114-N, 127-Y, 137, 113-Y, 104-N, 131-N, 110-N, 137, 105-Y, 110-N, 110-N, 121-Y, 137, 131-Y, 114-N, 112-N, 110-N, 121-N, 110-N, 125-N, 110-N, 137, 114-Y, 121-N, 126-N, 127-N, 110-N, 104-N, 107-N
2) based on the hint "Caeser-loving friend", i assume it's a caeser cipher (i.e. ROTXX)
3) ASCII only goes up to 127 in base10. so since we have numbers in here greater than 137, we can assume the base is less than 10. Stripping the letters and using [cyberchef](https://gchq.github.io/CyberChef/)base 8 results in
VKRXOG_LW_KDYH_EHHQ_YLJHQHUH_LQVWHDG
SHOULD\IT\HAVE\BEEN\VIGENERE\INSTEAD[which is likely the flag](https://gchq.github.io/CyberChef/#recipe=From_Octal('Space')ROT47(-3)&input=MTI2LCAxMTMsIDEyMiwgMTMwLCAxMTcsIDEwNywgMTM3LCAxMTQsIDEyNywgMTM3LCAxMTMsIDEwNCwgMTMxLCAxMTAsIDEzNywgMTA1LCAxMTAsIDExMCwgMTIxLCAxMzcsIDEzMSwgMTE0LCAxMTIsIDExMCwgMTIxLCAxMTAsIDEyNSwgMTEwLCAxMzcsIDExNCwgMTIxLCAxMjYsIDEyNywgMTEwLCAxMDQsIDEwNw)